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Functionalized alkoxy arene diazonium salts from paracetamol

Bernd Schmidt1, René Berger, Frank Hölter

  • 1Universitaet Potsdam, Institut fuer Chemie, Organische Synthesechemie, Karl-Liebknecht-Strasse 24-25, D-14476, Potsdam-Golm, Germany. bernd.schmidt@uni-potsdam.de

Organic & Biomolecular Chemistry
|March 6, 2010
PubMed
Summary

A new one-flask method synthesizes arene diazonium tetrafluoroborates from aromatic acetamides. This convenient process simplifies the preparation of these valuable synthetic intermediates, requiring only filtration for isolation.

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
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